THE STEREOCHEMISTRY OF MALEOPIMARIC ACID AND THE LONG RANGE SHIELDING EFFECT OF THE OLEFINIC BOND

W. A. Ayer; C. E. McDonald; J. B. Stothers

doi:10.1139/v63-159

journal article May 01, 1963

THE STEREOCHEMISTRY OF MALEOPIMARIC ACID AND THE LONG RANGE SHIELDING EFFECT OF THE OLEFINIC BOND

W. A. Ayer C. E. McDonald J. B. Stothers

Canadian Journal of Chemistry Vol. 41 No. 5 pp. 1113-1126 · Canadian Science Publishing

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Abstract

Nuclear magnetic resonance studies of methyl maleopimarate and closely related derivatives clearly establish the stereochemistry of methyl maleopimarate and, consequently, levopimaric acid. An extension of this study to other related compounds, 22 in all, provides evidence, on the basis of an intercomparison of the chemical shifts for the angular methyl protons, to support the original suggestion by Jackman (Applications of NMR in organic chemistry. Pergamon, New York. 1959. Chap. 7) that the long range shielding effect of the olefinic linkage is analogous to that of the carbonyl double bond. Coupling constants and chemical shifts for some of the protons of the bicyclo[2.2.2]octene system present in these compounds are also discussed.

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Details

Published: May 01, 1963
Vol/Issue: 41(5)
Pages: 1113-1126
License: View

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Cite This Article

W. A. Ayer, C. E. McDonald, J. B. Stothers (1963). THE STEREOCHEMISTRY OF MALEOPIMARIC ACID AND THE LONG RANGE SHIELDING EFFECT OF THE OLEFINIC BOND. Canadian Journal of Chemistry, 41(5), 1113-1126. https://doi.org/10.1139/v63-159

THE STEREOCHEMISTRY OF MALEOPIMARIC ACID AND THE LONG RANGE SHIELDING EFFECT OF THE OLEFINIC BOND

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